I think never learning to enjoy oneself was a symptom of his generation. We think it’s sad but his peers would have thought him the bees knees. Your post is haunting in all that the things you don’t say imply.
I can’t comment about the failure to enjoy himself because I have inherited some of that problem from my mother. She was scared of looking forward to things. She was convinced that if she did something bad would happen. There’s so much character in your Dad’s face. He must have been really interesting to know.